Stepping onto the stage at 8:30 p.m. to a rousing welcome from the standing room-only crowd, Webb, who has made Hugh's Room a regular stop in recent years, greeted some familiar faces in the front rows before easing into the cascading, melancholy piano opening of "Highwayman," a 1977 song made famous by Highwaymen Johnny Cash, Waylon Jennings, Kris Kristofferson and Willie Nelson. While Webb is perhaps best known as a writer of reflective, often devastatingly sad songs, he is also a gregarious and generous storyteller, his sharp wit and self-deprecating streak on full display throughout the night. He was clearly in a chatty mood, taking a few minutes to discuss the 50th birthday of Canada's flag, Family Day and even quip about the singer/songwriter movement of the 1970s — that it was mostly "half-assed singing, half-assed songwriting."
For much of the evening, Webb wove songs into long stories about the composer's remarkable life. He took the audience on a journey from the plains of his native Oklahoma, where hearing Glen Campbell's "Turn Around, Look At Me" coming out of his portable transistor radio pushed a 14-year-old Webb to pray to be able to write a song half as good as that one and have Campbell record it — a prayer answered a mere five years later when "By the Time I Get to Phoenix" became Campbell's first major hit — to the front steps of Frank Sinatra's mansion, where Ol' Blue Eyes called a long-haired, fresh-from-Monterey Pop Webb a "weird freakin' kid," to the pubs of Ireland for several days of drinking black velvets (a mix of Guinness and champagne) and "looting and pillaging, and more looting and pillaging" with actor/director/singer Richard Harris.
In the end, only seven numbers were played in full over 110 minutes, but each one featured moments of breathtaking creativity: an evocative melody to close the longing, poignant "Galveston"; a slower tempo on "By the Time I Get to Phoenix," to which Webb's weathered voice added a new dimension that made it feel more about the passage of time than a reflection on romantic failure; a short tribute to Bill Miller, Sinatra's pianist for more than 50 years, amidst the unusual chord progressions of "Didn't We?" Webb even put his Grammy-winning arranging skills to work to divide the room into a surprisingly tuneful set of harmony singers on a version of "The Worst That Could Happen," a hit for the Brooklyn Bridge.
The encore drew to a close with a rearranged "MacArthur Park," the familiar melody only emerging after the song's uptempo, symphonic piano interlude to remind the audience not only that Webb's compositions pack more ideas in a few bars than many musicians do in entire careers, but that they had truly had the privilege of witnessing a master of his craft perform on this frigid Toronto night.